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By Anon.

She is the only woman I’ve ever made love to, though she’s had dozens of lovers. I am her “little boy” and this is our story. I was 19 and she was a friend of my mother’s. She was 39 and treated me like family. She would kid around with me and call me the “son she never had” and sometimes jokingly I would call her Mom. Sometimes she would have me over to her apartment and cook for me or we would watch TV or go for a swim.

Sometimes after a swim she would take a shower with the door open or change in front of me. Occasionally she would tease me and say “I’ll show you mine if you show me yours.” This always embarrassed me. After puberty I had stopped letting anyone see me naked. I was good looking, but under my bathing suit I had never developed like most guys my age and I looked like a little boy with hair. My whole family would tease me about being small down there because my younger brother had grown big like my dad. All this teasing had led me to be shy around girls.

One night after a swim, she had changed into her robe and we were sitting at the kitchen table alone together when she asked, “Have you ever had a girlfriend?”

I didn’t say anything because I hadn’t.

“You do like girls don’t you?” she asked.

I had quite an extensive collection of girl magazines so I told her, “Of course.”

“Are you a virgin? You are! Aren’t you?” Then she said, ‘Why would a healthy 19 year old still be a virgin?”

I had to confess that I was embarrassed to be seen naked.

“Why?” she asked.

I reluctantly confided to her that I was embarrassed about having a small penis.

She looked at me for a moment, and then she said, “Follow me!” And we went into her bedroom. She sat on the edge of her bed and said, “Stand here in front of me. The best way for you to overcome your fears is to face them directly!”

Then she untied the string on my bathing suit and pulled it all the way down to my ankles. I was humiliated!

She smiled and said, “You are small, aren’t you!”

I wanted to die!

Then she said, “Sit next to me on the edge of the bed.”

I could see most of her breasts through the slit in her robe when she got on her knees and put my stiff little cock all the way into her mouth. I almost fainted then and there! Then she licked my nuts, then put me in her mouth again and ran her lips up and down around my entire length.

I quickly came in her mouth and she swallowed everything I had. Then she opened her robe and showed me her breasts.

Her breasts were creamy white with large aureoles and nipples that were a deep pink and hard. She had breast like the women in the magazines, they looked
great. She rolled her left nipple between her thumb and finger then she shoved her nipple in my mouth. “Suck me!” she commanded.

I was touching and sucking a woman’s breast for the very first time!

She started moaning and placed my hand between her legs. She was so wet! I put a finger inside her then I had two fingers inside of her. Next I was rubbing her swollen pussy with my whole hand. She laid down flat on the bed with her legs wide open, feet on the floor.

She had thick dark hair between her legs and her pink pussy lips were swollen and glistening, she said, “Eat me!” I started to lick her swollen opening. She held herself open as wide as she could while I licked her inner thighs and worked my way up, sticking my tongue as deep as it would go inside of her when she showed me the magic place she wanted me to lick.

“Gently, barley touch me there with your tongue,” she said. She moaned and a little later her whole body trembled. She held my face tight against her and
said, “Not bad for your first time though technically you’re still a virgin. Lets play a little game,” She said. “If you can put yourself inside of me then I’ll let you fuck me.”

Then she lay on her back with her legs closed tightly together. Her pussy lips were still swollen, which exposed her pink inner lips to me. I eased myself on top of her, and then easily slipped myself inside of her. We slowly turned over with her on top of me with her legs held tightly closed together with my legs spread open under her. Then she laughed and said, “You fuck like a girl.” That’s how we made love for the first time.

After that time we started seeing more of each other regularly. She told me she had special plans for me. “I knew you had never been with a woman.” She said. “Your mother told me that you were very shy around girls. She also mentioned that you had never fully developed.”

Then she held my hand and said, “It’s ok. You can trust me. Some women can be very cruel when it comes to men with small penises, I don’t want you to get hurt. I’ll protect you and teach you how to be a great lover.”

My secret was out and there was someone who accepted me. She said, “I want you as my boyfriend but remember: don’t ever embarrass yourself by trying to be with another woman.” Then she went on to say, “I want you to experience everything! We’ll start from the beginning. Remember when you were a little boy how you felt no shame, I want you to feel like a little boy again!”

She ran a cold bath and told me to get in. “Look at my little boy,” she said, “… little boys shouldn’t have hair down there.” She had me sit on the edge of the tub and completely covered my crotch with shaving cream. She started shaving my nuts and worked her way to my pubic area. When she was finished I was completely bare. I rinsed off in the now cold bath.

I felt humiliated and self-conscious about her seeing me small and bare and at the same time I felt completely free being so open and vulnerable to her.

Since then I always keep myself bare for her, she knows I could never be with another woman.

“Don’t ever worry about being too small to please me.” She showed me some pictures of nude men from her women’s magazine and compared them to a picture she’d taken of me. “Look how much different those men look than you, don’t try to compare yourself to other men, remember you’re not like them.”

I still get a little embarrassed when I see pictures of me compared to other men, but she says, “Don’t worry you’ll always be my little boy…”